First Night in Town
by Chris Halliwell's Lover
Summary: Takes place during Nick and Nora, this is what I think should have happened if Rory had snuck out with Jess, mature content!
1. Sneaking Out

Disclaimer: I don't own Gilmore Girls

Sorry that I kept changing tenses between past and present, I have a problem with that.

"Does this window open?" Jess Mariano asks. He and Rory are standing in her room. Lorelai, Luke, Sookie and Jackson are all in the living room preparing to start eating.

"Yes," Rory responded, slightly nervous because she could hear her mom calling, "But the food is ready, we should go."

"I agree one hundred percent," Jess said as he opened the window and gestured towards it, "We should go."

"I don't know," Rory hesitated, "There isn't anything to do in Stars Hallow at this time of the night."

"So what, let's go anyway," Jess was halfway through the window at this point, "I can think of a few things that we could do. Let's go." Jess repeated and offered Rory his hand.

"Alright," Rory said, glancing over her shoulder at the same time, "Just let me get my coat."

They were out of the house now, and Rory wasn't sure if this was the best idea after all and glanced back at the house. She could see Jackson, Sookie, Luke and her mom heaping food onto their plates. Jess saw Rory look and quickly grabbed her hand and pulled her along, "Let's get out of here." At the contact, Rory suddenly forgot all of her doubts and started running, this time pulling Jess along.

They ran as fast as they could until they ended up, out of breath, in the town square. Clinging to each other for support, they stood next to the gazebo to catch their breath. As soon as Rory is able she says, "I've never done anything like that before. It was exhilarating!"

"What?" Jess teased, "You've never sprinted until you were out of breath before?"

"Ha ha" Rory pretended to laugh, "So what should we do now? This was your idea and I'm bored."

Jess hesitated, "Do you want to get some food? We left before we had a chance to eat."

"Oh, so now you're concerned for my well being. Before you didn't seem to care if I ate or not."

"Well excuse me for wanting to eat with you and you alone." Jess added suddenly serious. At this comment, Rory blushed slightly, suddenly aware of what Jess had in mind for the evening. But she decides that she doesn't care. Dean doesn't thrill her the way this guy she just met a couple of hours ago does.

"Alright," Rory smiled flirtatiously, "Lead the way." Jess started walking across the street and down the sidewalk. He didn't say anything as Rory caught up with him. His plan had been to hook up with this girl and then never see her again, like all the others. But now, he was realizing just what kind of town he had come to. Rory obviously lived a very sheltered life, the girl hadn't even snuck out of her house before. Jess figured that eating would be the safest way to go; he wouldn't be as tempted to kiss her if they were alone. But just as they were walking past the movie theater that wasn't really a movie theater, Rory grabbed Jess and pulled him inside. For a fleeting moment he though she was going to kiss him. Jess's heart hammered at the thought of kissing this beautiful girl, but then he saw the worried expression on her face. "Rory, what's wrong?"

"Nothing, there was just someone I didn't want to see out there." Rory had just seen her boyfriend Dean walking across the street from them. She doesn't know why she doesn't want Dean to see her with Jess, it isn't like they are doing anything wrong. But maybe she wants to. "Look, Kirk's asleep, we can watch the movie for free."

Rory saw Jess smirking as they sat down in the back row to watch some old black and white movie, "What are you smiling about?"

"I just didn't take you for the sneak-into-the-movies-without-paying kind of girl. But then again, I didn't actually believe that you would leave the house in the first place."

"Well, there's a lot you don't know about me."

They spent the next hour watching the movie, but when Kirk started yelling in his sleep, they decide it would be best to leave. "So how about that food?" Jess asks as they walk out the door, "I saw a place that we can pick up a couple of slices of pizza when I was walking around this afternoon. Is it any good?"

"It's alright, but I think we should get a couple of pizzas, not just slices."

"Somebody likes to eat." Jess teases as they walk to the restaurant.

When they get to Al's Pizza world, a little counter-service version of Al's pancake world, the place is packed, so Jess orders the pizza and Rory goes to get a table. As she's walking she hears her name being called. Lane is standing outside waving for Rory to come outside. Rory obliges her longtime friend and abandons the search for a table.

"Lane, what's the matter?"

"I was just wondering if you would give me a slice of pizza when your mom brings it out. I'm starving! Where is your mom anyway? I don't see her in line."

"I'm not here with my mom, Lane. I'm her with Luke's nephew, Jess." Rory nervously replies, " Will you please just go and pretend that you never saw me if anyone asks? I kind of snuck out."

"You snuck out?!? I'm so proud. You're starting to act like me. But what about Dean?"

"I don't know. So far it's just been like two friends hanging out."

"But you want something to happen? Don't lie to me, I'm your best friend and I can tell when you're lying."

"Lane, I don't know. But I would like to see where this night goes."

"He is pretty hot. Alright, go make that guy fall in love with you."

"Lane!"

"Just kidding. I'm going. I'll even leave without any pizza."

"Who was that?" Jess asks Rory as she walks over to the table he found in the corner.

"Just my friend Lane"

The two ate in silence for the next fifteen minutes, mostly because Rory was starving and Jess could only stare at how much Rory was able to eat.

At one point, their legs accidentally brushed under the table and they both blushed and looked away.

Around eight o'clock, they head back outside to find something else to do. "Maybe we could go to Stars Hollow Books" Rory shyly suggested. "OK" Jess responded, confused by Rory's shyness, " There's this book I think you should read. I'll buy it for you." Pleased at Jess's response, she was afraid he would laugh at her, she smiled at him and forgot her shyness again.

Jess just found the book he plans to buy Rory, but now he can't find Rory. She had disappeared among the books soon after they had entered the shop. "Rory where are you?"

"I'm here!" She yelled back as she runs around the corner and straight into Jess and grabs onto him so that she doesn't fall. Just as she is about to apologize, Jess's lips are on hers, but just as suddenly they're gone.

"Sorry" Jess mumbles as he stumbles back from her, "I'm just going to go pay for this. I'll meet you outside."

Rory's slightly disappointed that Jess didn't keep kissing her, but pleased at the same time. He had kissed her! 'This is going to be a fun night.' Rory thought to herself.


	2. Reading

Warning: Rating went up this chapter due to sex-like scene.

I know Rory and Jess are going a lot faster than they would have on the show, but this Rory is supposed to be more like the season 5 Rory who undresses with Logan at her grandparents wedding.

"What do you say to going to read this book you bought me somewhere private?" Rory asks as she walks up to Jess, a little to close to him in his opinion.

"I guess that's a good idea. Where do you have in mind?"

"There's a bridge over there that no one ever uses." Rory points towards a wooded area with a barely visible path into it.

They have been walking along the path for about five minutes when their hands brush against each other, but this time, instead of blushing like when their legs touched, Jess grabs Rory's hand and doesn't let go. They walk for another five minutes and arrive at the bridge Rory had mentioned.

"Here sit down and I'll read out loud." Rory suggests and then leans against Jess once they are seated. As Rory reads, Jess's mind wanders. 'Rory smells delicious, like strawberries. Her hair is the color of maple syrup. And her neck. How I would love to kiss her neck.'

"Jess? Are you okay? You seemed like you were somewhere else." Rory tears Jess away from his daydream. As he becomes aware of reality again, he also realizes that he has been unconsciously twirling Rory's hair around his finger the whole time and that she didn't seem to mind. Then suddenly, Jess doesn't want his dream to just be a dream.

He kisses Rory lightly and then pulls back his head so that he can see her eyes. When he does see them, her eyes are so full of passion and longing that Jess can barely keep himself from ripping all of her clothes off and having his way with her right there. But he is able to control himself and states one simple word, in a deep, ragged voice "Rory." Instead of answering him, Rory is kissing Jess more fiercely than she has ever kissed anybody before.

The kissing goes on for a few minutes, but then Jess starts to want more. He removes his lips from Rory's ,causing her to moan at the loss of contact, but then moan in pleasure a moment later when Jess's lips are attacking her neck.

While Jess is busy with her neck, Rory decides to explore Jess's body. Her hands roam across his back and around to his stomach where she feels his chiseled abs and pecs and moans even louder. She wants Jess's shirt off so that she can feel his skin on hers. She starts to pull his shirt off, but has a little trouble so she moans out his name, "Jess" and he helps her.

When his shirt is off, Jess quickly kisses Rory and then let's his hands wander across her back and stomach. Then, after quickly looking at Rory for approval, takes her shirt off and tosses it next to his. After kissing Rory for a few more minutes, he starts kissing her chest above her bra.

The whole time, Jess and Rory had been sitting up, but now Jess lays Rory on her back so that he can kiss her stomach too. Hearing moans of approval from Rory, Jess begins to explore more of her body. He lightly brushes his hands over her bra and around to her back where he unlatches it. Glancing down at Rory, he sees that she's blushing. 'This is even worse than I first thought,' Jess thinks to himself, 'She's a virgin too. I'm falling for her and she's a virgin. I had only planned to hook up with her once. I'm such an idiot. Why did I have to pick her? I've slept with many girls after just knowing them a few hours. Whey am I falling for _her_?'

"Jess? Are you okay? You were off in your own little world again."

"Yeah, I'm fine" And to prove this, he starts nibbling on Rory's neck and massaging her breasts causing her to moan in pleasure. Encouraged by this, Jess takes one of her breasts into his mouth. Rory practically screams out due to the pleasure she's feeling. She and Dean had never gone this far and she's finding that she wants more, so she moans out Jess's name again.

When Jess hears this, he feels his hard erection getting even harder. He lets his hands wander down to her jeans and his lips move back to her neck. After he undoes the button on the jeans, Jess lazily trails his fingers just above the top of her panties causing Rory to shiver beneath him.

Jess's hesitancies about sleeping with a virgin whom he had just met vanished at this point due to the overwhelming need to make her scream out his name in pleasure during her climax.

Then, overcome by his own needs and wants, Jess dips a finger into Rory's panties and then inside her.

"Jess wait" Rory gasps out as soon as he does this, and Jess immediately jumps away from her, "I'm sorry Rory, I thought you wanted this."

"I do want this. It's just, wouldn't you rather do this in a bed?"

"Of course," Jess sighs in relief, Rory isn't going to start yelling and bring the whole town to her rescue, "But we can't go to your house or Lukes's."

"Jess, my mom owns an Inn. We can sneak in there." Rory says with a little smile.


	3. Blissful Night

**I still don't own Gilmore Girls! **

**More mature content this chapter.**

**Also, I tried to portray Jess and Rory more like they are on the show by showing their doubts, but does it work or is it annoying? Please review. And thanks to all of you who did review, sorry I haven't updated in forever!**

The Independence Inn is asleep for the night when Jess and Rory sneak in through a back door. "Rory, are you sure we won't get in trouble for breaking in, because we could get caught, and when I do something illegal, I make it a habit not to get caught."

"Jess, stop worrying," Rory says as she peers around the corner into the lobby where the room keys are, "I told you, the owner is like a second grandmother and my mom is the manager."

"No," Jess replies with a slight edge to his voice, "you told me you _mom_ is the owner. We'd better not get caught!"

"Don't worry Jess, I'll try not to scream too loudly" she says as she wiggles her eyebrows at the implication of her words, but inside she's wondering if she's being too bold and will regret the night later. After all, she had just met Jess this afternoon and she has a boyfriend. Rory muses to herself, _'But Dean isn't nearly as good of a kisser as Jess, and I've never felt this way about Dean. I haven't even thought about sex with him, let alone come close to it, so if I want to have sex with Jess I must really like him. Jess seems like a nice enough guy. Besides, what harm can it do? I think I'm falling in love with Jess anyway. Wait, did I just think that? This is not good. I just need to let go and have some fun for once in my life.' _

While Rory had been thinking, Jess had snuck behind the front desk and grabbed the nearest room key. As soon as Rory implied that they would be having sex, his body had taken over and he forgot all of his concerns about being with Rory so quickly.

"Come on Rory," Jess murmurs as he gives Rory a quick kiss, "I have the key to room eight." They try to sneak upstairs quietly, but are constantly kissing and touching each other. It takes even longer to open the door due to them having to separate so that Jess can get to the door. As soon as they're in the room, they're all over each other again.

Jess kisses Rory deeply as he lays her down on the bed. He licks her lower lip asking for entrance, which is immediately granted. Jess's tongue battles with Rory's, but he can tell that she's somewhat hesitant about this. He thinks, _'I hope this is not the first time Rory's ever kissed with tongue. She can't be that inexperienced.' _Rory thinks, _'I hope I'm good enough for Jess; he seems very experienced. I also hope he has some protection because mom didn't end up making me go on the pill after that fiasco with Dean after the dance. Dean. I need to stop thinking about him.' _

In order to stop thinking about Dean, Rory put as much passion as she can into the kiss while reaching down to remove Jess's shirt. This is all the encouragement he needs to resume his exploration of Rory's body after helping her remove his own shirt and hers.

Jess kisses Rory's neck and sucks on the tender spots he had found before.

Rory twines her hands in his hair and enjoys the pure bliss that is Jess's lips. Soon her bra joins the other articles of clothing on the floor, and Jess is sucking and massaging her breasts causing Rory to moan in pleasure. He then makes his way down her stomach, removes her jeans and then returns to kissing her stomach. When he reaches the top of her panties, he hesitates slightly, but then sticks his finger into her folds for the second time that night. Hearing moans of approval, he removes her panties and continues to pleasure Rory with both his finger and his tongue. She squirms under his touch and pushes her hips up towards him, moaning the whole time. He pushes his finger in one last time and Rory reaches her orgasm. The feelings of pleasure are like nothing that she has ever felt before.

As soon as Rory recovers slightly, she moans Jess's name nearly causing him to lose his mind at the ragged tone of wanting. He quickly pulls off his pants and boxers. At the last second, he remembers that Rory is a virgin, and he restrains himself so that he doesn't hurt her. Rory nods her consent and he gently enters her.

They have sex two more blissful times that night, even though Jess knows that Rory will be sore in the morning, but he can't help himself. After Rory falls asleep in Jess's arms, he whispers to her, "Even though I've only known you for one day, I love you. I've never told a girl that before and meant it." He kisses her on the cheek and then falls asleep, but worry does not feel or hear anything.

The sun wakes the pair up the next morning. Rory yawns and looks for her alarm clock, but it's not there. Startled, she looks around and doesn't see her own room, but then she spots Jess and remembers the completely wonderful night they had together, including the not so wonderful part where she and Jess snuck out. "Jess, wake up! We have to go home. My mom and Luke must be going crazy looking for us and it's only a matter of time before they decide to look here and we do not want to get caught!" Jess's only response to this is to reach over and pull Rory, who had been searching for her panties, back into bed and kissing her deeply.

As soon as they come up for air Rory tries again, "Jess, if the town finds out I lost my virginity to you, they will hunt you down, draw and quarter you and then hang you from the gazebo. Get up!" At the this, Jess jumps out of bed mumbling something about the town psychos thinking they were still living in 1750.

After dressing, Rory and Jess quietly sneak down the stairs and out the same door they had come through the night before. They walk around all of the places where they might run into other people who would inform Luke and Lorelai of where the two had been.

When they get to the street where turning left would lead to Rory's house and right would lead to Luke's, Rory stops to say goodbye to Jess. "So, if you go right it'll take you back to Luke's. I guess I'll see you later."

"You think I'm just going to dump you in the middle of the street?" Jess asks shocked, "After an amazing date with a girl I really like, I usually take her home."

"First of all Jess, this unfortunately wasn't a date and secondly, you really like me?"

"Alright, you have me there, and yes I really like you. Now let's go." Jess commands as he takes Rory's hand and leads the way to her house.

The Jeep is gone when Rory and Jess get to her house, (Lorelai is out looking for Rory) so Jess walks Rory up to the front door, "Do you want to go out on a real date next Saturday Rory?"

"I'd love to go on a real date. Do have any cute friends I could go out with?" She jokes.

"Ha ha very funny." Jess fake laughs, "I was thinking we could go out." At this point Rory remembers Dean and her mom again and nearly chokes at the thought. "Are you okay?" Jess asks startled.

"Yes, I just need to call my mom. She must be worried sick!" Rory is back to her old self and the girl from last night is gone, "I'll see you around Jess. Don't tell anyone about us please!" She gives him a quick kiss on the cheek and rushes into her house to salvage her now damaged life.

**End. I know it's somewhat abrupt, but I'll work on a sequel. **


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